1-Ethylpiperazine → 1-Cyclopropyl-8-(4-ethyl-1-piperazinyl)-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 981225Notes

Reaction equation

HRID 981225 reaction equation
Cl[C:2]1[C:3]([F:23])=[CH:4][C:5]2[C:6]([CH:22]=1)=[N:7][C:8]1[N:9]([CH:19]3[CH2:21][CH2:20]3)[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[CH2:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[CH3:25]>N1C=CC=CC=1>[CH:19]1([N:9]2[C:8]3[N:7]=[C:6]4[CH:22]=[C:2]([N:29]5[CH2:30][CH2:31][N:26]([CH2:24][CH3:25])[CH2:27][CH2:28]5)[C:3]([F:23])=[CH:4][C:5]4=[CH:14][C:13]=3[C:12](=[O:15])[C:11]([C:16]([OH:18])=[O:17])=[CH:10]2)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 791961-EthylpiperazineHCID 147005568-Chloro-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 147005761-Cyclopropyl-8-(4-ethyl-1-piperazinyl)-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acidYield 27.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Cyclopropyl-8-(4-ethyl-1-piperazinyl)-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is prepared under the conditions of Reference Example 5 but starting from 2 g of 8-chloro-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid and 2.74 g of 1-ethyl-piperazine in 20 cm3 of pyridine. The pure product is isolated after a first recrystallization from 105 cm3 of ethanol containing 25% of dimethylformamide followed by a second recrystallization from 75 cm3 of ethanol containing 50% of dimethylformamide. 0.67 g of 1-cyclopropyl-8-(4-ethyl-1-piperazinyl)-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is obtained in the form of a yellow-green solid melting at 254° C.

Workup

  1. custom1-Cyclopropyl-8-(4-ethyl-1-piperazinyl)-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is prepared under the conditions of Reference Example 5
  2. customThe pure product is isolated
  3. customafter a first recrystallization from 105 cm3 of ethanol containing 25% of dimethylformamide
  4. customfollowed by a second recrystallization from 75 cm3 of ethanol containing 50% of dimethylformamide

Sources & evidence

ORD record
ord-f5163607bf1a40bd8b24e5bc890f0d01
Source dataset
uspto-grants-1991_02
Patent number
US04990515

Reaction notes

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